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Antimicrobial activity of novel isothiuronium salts with 7-chloro-4,6-dinitrobenzofuroxan-5-olate anion

, 
Dmitriy Il'gizarovich Bakhtiyarov 1
Dmitriy Il'gizarovich Bakhtiyarov
, 
Luiza Magdanurovna Usupova 2
Luiza Magdanurovna Usupova
, 
Alexander Vladimirovich Gerasimov 1
Alexander Vladimirovich Gerasimov
, 
Marina Petrovna Shulaeva 3
Marina Petrovna Shulaeva
, 
Oskar Kimovich Pozdeev 3
Oskar Kimovich Pozdeev
, 
Ahat V Ilyasov 4
Ahat V Ilyasov
, 
Daut Rinatovich Islamov 1
Daut Rinatovich Islamov
, 
Konstantin Sergeyevich Usachev 5
Konstantin Sergeyevich Usachev
,  , 
Vladimir Ivanovich Galkin 1
Vladimir Ivanovich Galkin
10.1016/j.mencom.2021.04.027
Published 2021-04-28
Communication , Volume 31, Issue 3, 365-367
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Galkina I. V. et al. Antimicrobial activity of novel isothiuronium salts with 7-chloro-4,6-dinitrobenzofuroxan-5-olate anion // Mendeleev Communications. 2021. Vol. 31. No. 3. pp. 365-367.
GOST all authors (up to 50) Copy
Galkina I. V., Bakhtiyarov D. I., Usupova L. M., Gerasimov A. V., Shulaeva M. P., Pozdeev O. K., Ilyasov A. V., Islamov D. R., Usachev K. S., Bakhtiyarova Y. V., Galkin V. I. Antimicrobial activity of novel isothiuronium salts with 7-chloro-4,6-dinitrobenzofuroxan-5-olate anion // Mendeleev Communications. 2021. Vol. 31. No. 3. pp. 365-367.
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TY - JOUR
DO - 10.1016/j.mencom.2021.04.027
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.04.027
TI - Antimicrobial activity of novel isothiuronium salts with 7-chloro-4,6-dinitrobenzofuroxan-5-olate anion
T2 - Mendeleev Communications
AU - Galkina, Irina Vasilievna
AU - Bakhtiyarov, Dmitriy Il'gizarovich
AU - Usupova, Luiza Magdanurovna
AU - Gerasimov, Alexander Vladimirovich
AU - Shulaeva, Marina Petrovna
AU - Pozdeev, Oskar Kimovich
AU - Ilyasov, Ahat V
AU - Islamov, Daut Rinatovich
AU - Usachev, Konstantin Sergeyevich
AU - Bakhtiyarova, Yulia Valerievna
AU - Galkin, Vladimir Ivanovich
PY - 2021
DA - 2021/04/28
PB - Mendeleev Communications
SP - 365-367
IS - 3
VL - 31
ER -
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@article{2021_Galkina,
author = {Irina Vasilievna Galkina and Dmitriy Il'gizarovich Bakhtiyarov and Luiza Magdanurovna Usupova and Alexander Vladimirovich Gerasimov and Marina Petrovna Shulaeva and Oskar Kimovich Pozdeev and Ahat V Ilyasov and Daut Rinatovich Islamov and Konstantin Sergeyevich Usachev and Yulia Valerievna Bakhtiyarova and Vladimir Ivanovich Galkin},
title = {Antimicrobial activity of novel isothiuronium salts with 7-chloro-4,6-dinitrobenzofuroxan-5-olate anion},
journal = {Mendeleev Communications},
year = {2021},
volume = {31},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.04.027},
number = {3},
pages = {365--367},
doi = {10.1016/j.mencom.2021.04.027}
}
MLA
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Galkina, Irina Vasilievna, et al. “Antimicrobial activity of novel isothiuronium salts with 7-chloro-4,6-dinitrobenzofuroxan-5-olate anion.” Mendeleev Communications, vol. 31, no. 3, Apr. 2021, pp. 365-367. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.04.027.

Keywords

antimicrobial activity
benzofuroxan-5-olates
hydrolysis
isothiuronium salts
nitroarenes
X-ray diffraction

Abstract

New thermally stable long-chained 2-alkylisothiuronium 7-chloro-4,6-dinitrobenzofuroxan-5-olates were obtained from the corresponding bromides and 5,7-dichloro-4,6-dinitrobenzofuroxan, the hydrolysis of the C(5)–Cl bond to produce phenolic function having occurred in the course of the process. The compound structure was determined by IR spectroscopy, elemental analysis and X-ray single crystal study. Salts with C14–C18 alkyl groups revealed moderate antibacterial and antifungal activities.

References

2.
Synthesis, Structure, and Antimicrobial Activity of the Reaction Products of Chloronitro-Substituted Benzofurazanes and Benzofuroxanes with Morpholine
Galkina I.V., Takhautdinova G.L., Ivshin K.A., Yusupova L.M., Krasnyuk I.I., Egorova S.N., Shulaeva M.P., Pozdeev O.K., Kataeva O.N., Galkin V.I.
Russian Journal of General Chemistry, 2017
3.
An Unusual Reaction of Triphenylphosphine with Dichlorodinitrobenzofuroxan
Galkina I.V., Tudriy E.V., Kataeva O.N., Yusupova L.M., Luftmann H., Galkin V.I.
Phosphorus, Sulfur and Silicon and the Related Elements, 2009
5.
Synthesis, structure, and antibacterial activity of aminobenzofuroxan and aminobenzofurazan
Galkina I.V., Takhautdinova G.L., Tudrii E.V., Yusupova L.M., Falyakhov I.F., Pozdeev O.K., Shulaeva M.P., Kipenskaya L.V., Sakhibullina V.G., Krivolapov D.B., Litvinov I.A., Galkin V.I., Cherkasov R.A.
Russian Journal of Organic Chemistry, 2013
6.
Cardiovascular actions of the furoxan CAS 1609, a novel nitric oxide donor
Bohn H., Brendel J., Martorana P.A., Schönafinger K.
British Journal of Pharmacology, 1995
7.
Thiol-mediated generation of nitric oxide accounts for the vasodilator action of furoxans
Feelisch M., Schönafingeri K., Noack H.
Biochemical Pharmacology, 1992
8.
Mutagenesis by 4-nitrobenzofurazans and furoxans
Macphee D.G., Robert G.P., Ternai B., Ghosh P., Stephens R.
Chemico-Biological Interactions, 1977
9.
1,2,5-Oxadiazole N-Oxide Derivatives and Related Compounds as Potential Antitrypanosomal Drugs:  Structure−Activity Relationships
Cerecetto H., Di Maio R., González M., Risso M., Saenz P., Seoane G., Denicola A., Peluffo G., Quijano C., Olea-Azar C.
Journal of Medicinal Chemistry, 1999
10.
Synthesis and antimycobacterial activity of new quinoxaline-2-carboxamide 1,4-di-N-oxide derivatives.
Zarranz B., Jaso A., Aldana I., Monge A.
Bioorganic and Medicinal Chemistry, 2003
11.
Synthesis and biological evaluation of novel structural hybrids of benzofuroxan derivatives and fluoroquinolones
Chugunova E., Akylbekov N., Bulatova A., Gavrilov N., Voloshina A., Kulik N., Zobov V., Dobrynin A., Syakaev V., Burilov A.
European Journal of Medicinal Chemistry, 2016
12.
New 3,4-bis(indol-1-yl)maleimides as protein kinase inhibitors
Panov A.A., Lakatosh S.A., Kubbutat M.H., Dezhenkova L.G., Totzke F., Schechtel K.
Chemistry of Heterocyclic Compounds, 2019
13.
Benzofuroxans: their synthesis, properties, and biological activity
Chugunova E.A., Gazizov A.S., Burilov A.R., Yusupova L.M., Pudovik M.A., Sinyashin O.G.
Russian Chemical Bulletin, 2019
14.
Isothioureas as Germicides
Bandelin F.J., Tuschhoff J.V.
Journal of the American Chemical Society, 1952
15.
90. Antituberculous compounds. Part V. 2-Sulphanilamido-5-alkyl-1 : 3 : 4-oxadiazoles and -thiadiazoles and related isothiosemicarbazones and isothioureas
Brooks J.D., Charlton P.T., Macey P.E., Peak D.A., Short W.F.
Journal of the Chemical Society (Resumed), 1950
16.
S‐Aryl(tetramethyl)isothiouronium Salts as Possible Antimicrobial Agents, I
Bella M.D., Tait A., Parenti C., Bondi M., Quaglio G.
Archiv der Pharmazie, 1986
17.
10.1016/j.mencom.2021.04.027_bib0085
Keera
J. Sci. Ind. Res., 2002
20.
Surface and biocidal activity of some synthesized metallo azobenzene isothiouronium salts.
Badawi A.M., Azzam E.M., Morsy S.M.
Bioorganic and Medicinal Chemistry, 2006
22.
Allylic isothiouronium salts: The discovery of a novel class of thiourea analogues with antitumor activity.
Ferreira M., Assunção L.S., Silva A.H., Filippin-Monteiro F.B., Creczynski-Pasa T.B., Sá M.M.
European Journal of Medicinal Chemistry, 2017
23.
Alexeev A.A., Nurieva E.V., Trofimova T.P., Chesnakova E.A., Grishin Y.K., Lyssenko K.A., Filimonova M.V., Zefirova O.N.
Mendeleev Communications, 2019
24.
Introduction of isothiuronium surfactant series: Synthesis, structure-dependent aggregation overview and biological activity
Valeeva F.G., Karimova T.R., Pavlov R.V., Bakhtiyarov D.I., Sapunova A.S., Ivshin K.A., Kataeva O.N., Gaynanova G.A., Syakaev V.V., Voloshina A.D., Galkina I.V., Latypov S.K., Zakharova L.Y.
Journal of Molecular Liquids, 2021
25.
OLEX2: a complete structure solution, refinement and analysis program
Dolomanov O.V., Bourhis L.J., Gildea R.J., Howard J.A., Puschmann H.
Journal of Applied Crystallography, 2009
26.
10.1016/j.mencom.2021.04.027_bib0130
Sheldrick
Acta Crystallogr., 2015
27.
10.1016/j.mencom.2021.04.027_bib0135
Sheldrick
Acta Crystallogr., 2007
28.
Mercury: visualization and analysis of crystal structures
Macrae C.F., Edgington P.R., McCabe P., Pidcock E., Shields G.P., Taylor R., Towler M., van de Streek J.
Journal of Applied Crystallography, 2006